Failure is part of the development process in analysis and psychotherapy, and, by implication (and taken up a level), the study of failure in broad terms will be part of the development of the profession going forward. The analyst and therapist must give up the rescue fantasy, give up being right and justified, give up misplaced ambition, but also give up guilt, self-blame, and disappointment, and embrace an approach in which the interpretation of the pathogenic situation of early childhood (in which traumatic deidealization of the parent occurred), becomes inherently transformative. It reactivates the process of structure-building internalization. Learning to live within one’s limitations invites a process of risk taking that sometimes results in failure and sometimes results in—redefining one’s limitations outwards towards an endless horizon of progress in satisfaction and meaning making. Our thanks to Arnold Goldberg both for the journey and the end result.